Gold succinimide compound and process of making the same



Patented Aug. 18, 1931 PATENT OFFICE WILLIAM JACKSON POPE, or CAMBRIDGE, ENGLAND GOLD SUCOINIMIDE COMPOUND AND PROCESS OF MAKING THE SAME No Drawing. Application filed October 11, 1930, Serial No. 488,186, and in Great Britain July 19,1929.

The invention relates to the manufacture of gold compounds of succinimide, which can be used as drugs when it is desirable to administer gold compounds in which the gold is not in the form of the auric or aurous ion.

The compounds in question are obtained by the interaction of gold hydroxide or chloroauric acid or one of their salts, or fulminating gold, with succiniinid e and a base at a suitable temperature in presence, when necessary,

of a solvent. The compositionof the resulting compound can be varied by varying the temperature and the proportions of the reacting substances and solvents. The compounds obtained are of the nature of so-called co-ordinated gold compounds and in stating their composition it is convenient to use the conventional method of formulating the compo 'sitions of the co-ordinated metallic compounds, without, however, binding myself to the accuracy of such method of formulation.

Using the method of manufacture stated above in general terms, the following gold derivatives of succinimide, amongst others,

have been prepared ion, such as the co-ordinated group [Ausu or [CI AuSu L].

It is perhaps desirable to note that water or other solvent of crystallization is not included in the above formulae.

By the present invention it is possible to obtain'for the firstt'ime gold derivatives of succinimide, and it is to be understood that obliquely tuncated water-clear prisms.

chloride in water.

the scope of the invention is intended to embrace all such derivatives obtained by any of the methods above described or their obvious chemical equivalents.

The following examples will further illustrate how the invention may be carried out in practice, but the invention is not limited to these examples.

Example 1.Preparation,and properties of the compound [(NH-g) AuSu C1.

A mixture of chloroauric. acid (=3 g. of metallic gold), succinimide', and 20 cc. of alcohol is treated with sufiicient aqueous andmonia to neutralize the acid present. Heat is then applied, if necessary, to effect com. plete dissolution of thesuccinimide. The remainder of the base, making 6 cc. of ammonia (d=.880) in all, is then added drop by drop. The whole is set aside to crystallize, and the crude product filtered off. This is ground up with 15 cc. of cold water, which extracts a quantity of -more P soluble products, leaving 5 g. of the salt,'[NH AuSu ]Cl. This is soluble to the extent of 12% in cold water; it dissolves readily in boiling water containing a little succinimide, but only a small amount crystallizes out unchanged, the rest being transformed into other compounds. The pure chloride forms characteristic Example .2.The aurichloride,

. AllSll is prepared by double decomposition, using theoretical quantities of the chloride described in Example 1 and of sodium auri- It forms bright yellow prisms, which are almost insoluble in water. Eazample 3.Preparation and properties of the compound [(CH NH AuSu ]Cl. This preparation is carried out in the same manner as in Example 1, except that 15 cc. of alcohol is used as the solvent and 9 g. of 33% aqueous methylamine replaces the ammonia. The crude product is more soluble in-water (810%) than is the corresponding ammonia analogue. The bromide,

omnrrzj m suger," and the aurichloride are sparingly soluble salts, easily obtained pure by double decomposition from the chloride.

Example 4.Preparation and properties of the compound [NHEt AuSu Cl.

This compound is prepared as described for the ammonia derivative above, except that 5 0 cc. of alcohol is used as the solvent and the ammonia is replaced by 6 ccof anhydrous diethylamine. The crude product is washed with cc. of water (filtrate A). The residue is practically pure chloride, [(NHEt AuSu ]Cl, weight 4.35 g. It is soluble in parts of cold, and 12.5 parts of hot water and separates from the latter on cooling in needles. The corresponding bro- -mid'e, thiocyanate, and auri'chloride are sparingly soluble compounds formed by. double "decomposition, using the theoretical quantities. The filtrate A (above) deposits on standing massive colourless crystals which consists: of the aurosuccini-mide of the complexionr, [(NHEtQgAuSm} [AuSu The filtrate A also contains diethylamine aurosuccin-ianide. In order to obtain this compound in. quantity themethod of preparation is somewhataltered. The chloroauric acid, succinimide, and alcohol are heated to boiling and 4 g. of diethylamine is added. The chloride, (NHEtg Ausufl cl, which is precipitated, is'filteredl from the hot solution -which is-then treated with a further 4- cc. of da'rethylam-ine. The lustrous leaflets which separate- 'on cooling may be recrystallized from alcohol giving pure diethylamine aurosuccinimide, NHEt HAuSu E a ample 5."(i) Preparation and properties of the compound [NI-LAuSufl The substanceis obtained by boiling a solution of 1gof the compound per-like appearance.

' Aus-u Cl,

' and 1 g. of succinimide in 5 cc. of water until the product which separates on cooling is freeiromhalogen (10I5 minutes).

It may be recrystallized from water, preferably with the addition of alcohol or acetone. It forms white exceedingly fine needles, which, on drying, assume a silky or pa- It may be heated to ltl0 /l5 mm. Without loss of weight. It is "soluble water to the extent of about 3% at the ordinary temperature. VV'hen prepared -'-by the abo emethod 6' g. of gold afl'ord about 9 g", of pure crystalline product.

(it) A second method is avail-able by which I this compound may be obtained directly in one operation.

3 of gold in the form of chloroauric acid is dissolved in'about 500 cc. of water and precipi tated with ammonia. gold is filtered often an asbestos mat, washed with water and with alcohol and transferred to a 7 5 cc beaker with 8 g. of succinimide, 14 cc. of water and 30 drops of ammonia. The mixture is warmed on the water bath unsoluble in acetone.

The fulminating' Example 8.-The

til :1 clear dark red solution results. An equal volume of alcohol is added and the product allowed to crystallize. The solid matter is filtered ofi and recrystallized as described above.

Example 6.Preparation and properties of the compound [CH NH AuSu This substance is obtained from the compound [(CH NH AuSu Cl by heating it with succinimide in aqueous alcohol. It crystallizes in short needles and is more soluble in Water and aqueous alcohol than the ammonia derivative. 7

E mample '7.The acid H [AuSu and its salts.

' The. diethylami-nesalt of this acid has already been described. The trimethylamine salt NMe HAuSu H O, is obtained by the action. of 6 g. of trimethylamine (33% aqueous) on chloroaunc acid (=3 g. of

metallic gold), succinimide (8' g.) and alcohol (12 cc.).. The solution becomes colourless when the addition of the trimethylamine is completed. On addition of 100' cc. of acetone, white crystalline leaflets separate. These are purified by recrystallization from a mixture of 10 cc. of alcohol and 5 cc. of acetone. They are exceedingly soluble in water, readily soluble in alcohol and slight- The aqueous solution decomposes on boiling, liberating metallic gold and the crystals turn purple on exposure to the light.

(ii) The triethylamine salt was prepared similarly and had similar properties.

(iii) The free acid is obtained by adding hydrochloric acid to an aqueous solution of one of the salts, when'beautiful silky needles are precipitated. These consist of the free acid, HAuSu which probably crystallizes (iofThe potassium salt, KAuSu is ob-- tained from a solution of the acid in a little water with the calculated quantity of alcoholic potash. It is very soluble in water but easily salted out by potassium salts.

('U) The sodium salt, NaAuSu is easily precipitated by salting out from aqueous sc lutions. It is also formed directly by the action of sodium ethoxide on chloroauric acid and succinimide in alcoholic solution. It crystallizes in needles.

salts Na[Cl AuSu and K[Cl AuSu These compounds are formed by the ac- .tion of alkali hydroxides or carbonates on chloroau-rio acidand succinimide in aqueous or alcoholic solutions. They are pale yellow in colour and very readily soluble in Water. With barium chloride they yield sparingly soluble pale yellow leaflets of the barium salt.

What I claim and desire to secure by Letters Patent is 1. A process for the preparation of gold compounds of succinimide consisting in the interaction in an aqueous solution of succinimide with an inorganic gold compound and a non-cyclic nitrogen base.

2. A process for the preparation of gold compounds of succinimide consisting in the interaction in an aqueous solution of succinimide with a reactive inorganic gold compound and ammonia.

3. A process for the preparation of gold compounds of succinimide consisting in the interaction in an aqueous solution of succinimide with a reactive inorganic gold compound and an alkyl amino.

4.- An ammonium gold succinimide.

5. An alkyl amino gold succinimide.

6. A compound of a non-cyclic nitrogen base, gold and succinimide.

In testimony whereof, I aifix my signature.

WILLIAM JACKSON POPE. 

